3-Ethyl-1-pentyn-3-ol → HCID 59774901, compound

HRID 2422570Notes

Reaction equation

HRID 2422570 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:11][C:12]([C:16]#[N:17])=[N:13]2)=[CH:8][CH:7]=1)=[N+:2]=[N-:3].[CH2:24]([C:26]([OH:31])([CH2:29][CH3:30])[C:27]#[CH:28])[CH3:25].C(N(C(C)C)CC)(C)C>C1COCC1.[Cu](I)I>[CH2:27]([C:26]([C:24]1[N:3]=[N:2][N:1]([CH2:4][CH2:5][C:6]2[CH:15]=[C:14]3[C:9]([C:10]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:11][C:12]([C:16]#[N:17])=[N:13]3)=[CH:8][CH:7]=2)[CH:25]=1)([OH:31])[CH2:29][CH3:30])[CH3:28]

Participants

6

Reactant 3

HCID 226983-Ethyl-1-pentyn-3-olHCID 81531DiisopropylethylamineHCID 59774904HCID 59774904, compound

Product 1

HCID 59774901HCID 59774901, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-(2-azidoethyl)-4-phenylquinoline-2-carbonitrile (128 mg, 0.43 mmol), 3-ethylpent-1-yn-3-ol (63 mg, 0.56 mmol), copper iodide (58 mg, 0.65 mmol) and diisopropylethylamine (375 μL, 2.2 mmol) in THF (5 mL) was stirred at rt for 6 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification on silica gel (eluting with acetone/dichloromethane, 2:8) gave the title compound. MS (+ESI): 394 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification on silica gel (eluting with acetone/dichloromethane, 2:8)

Sources & evidence

ORD record
ord-0f855391882948d89b9d2a68d63a1cdb
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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